Studies on Topical Antiinflammatory Corticosteroids. II. : Synthesis and Vasoconstrictive Activity of 11β, 17α, 21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione 17-Methoxy- and (Methylthio)acetates

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概要

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• 17-Methoxyacetate (3a) and 17-(methylthio)acetate (3b) of 11β, 17α, 21-trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6α-methylprednisolone, 1) and their 21-esters (4a and 4b) were synthesized and tested for vasoconstrictive activities. The activities of the 17-(methylthio)acetate derivatives (3b and 4b) were more potent than those of the corresponding 17-methoxyacetates (3a and 4a). The activities of 3b, 4a_2,4b_<1-4> and 4b_5 were equivalent to that of 9α-fluoro-11β, 21-dihydroxy-16β-methyl-17α-valeroyloxy-1,4-pregnadiene-3,20-dione (betamethasone 17-valerate, BV). The reaction of 6α-methylprednisolone (1) with triethyl orthomethoxyacetate afforded a stereoisomeric mixture of 6α-methylprednisolone 17,21-cyclic ortho esters (2aA and 2aB) in a ratio of 22 : 78,while the reaction of 1 with triethyl ortho(methylthio)acetate resulted in the formation of a single isomer (2bB) of the isomeric 17,21-cyclic ortho esters (2b).

• 社団法人日本薬学会の論文
• 1986-04-25

著者

• 池上 四郎

  Faculty of Pharmaceutical Sciences, Teikyo University

• 内藤 泰男

  Research Laboratories Ohta Pharmaceutical Co. Ltd.

• 梶原 良夫

  Research Laboratories Ohta Pharmaceutical Co. Ltd.

• 吉田 誠一郎

  Research Laboratories, Ohta Pharmaceutical Co., Ltd.

• 菅井 三郎

  Research Laboratories, Ohta Pharmaceutical Co., Ltd.

• 神原 俊文

  Research Laboratories, Ohta Pharmaceutical Co., Ltd.

• 赤星 三彌

  Research Laboratories, Ohta Pharmaceutical Co., Ltd.,

• 岡崎 徳二

  Research Laboratories, Ohta Pharmaceutical Co., Ltd.,

• 釜野 徳明

  Japan and Cancer Research Institute, Arizona State University

• 釜野 徳明

  Cencer Reseach Institute And Department Of Chemistry Arizona State University

• 赤星 三彌

  Research Laboratories Ohta Pharmaceutical Co. Ltd.

• 池上 四郎

  Faculty Of Pharmaceutical Sciences Teikyo University

• 吉田 誠一郎

  Research Laboratories Ohta Pharmaceutical Co. Ltd.

• 菅井 三郎

  Research Laboratories Ohta Pharmaceutical Co. Ltd.

• 神原 俊文

  Research Laboratories Ohta Pharmaceutical Co. Ltd.

• 岡崎 徳二

  Research Laboratories Ohta Pharmaceutical Co. Ltd.

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